Ring-Opening Polymerization of Prodrugs: A Versatile Approach to Prepare Well-Defined Drug-Loaded Nanoparticles

The synthesis of polymer–drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring‐opening polymerization. The monomers polymerize into well‐defined polymer prodrugs that are designed to...

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Bibliographic Details
Published in:Angewandte Chemie 2015-01, Vol.127 (3), p.1016-1020
Main Authors: Liu, Jinyao, Liu, Wenge, Weitzhandler, Isaac, Bhattacharyya, Jayanta, Li, Xinghai, Wang, Jing, Qi, Yizhi, Bhattacharjee, Somnath, Chilkoti, Ashutosh
Format: Article
Language:eng ; ger
Subjects:
Chemical compounds
Chemistry
Drug delivery systems
Drugs
Glycols
Krebstherapie
Monomers
Nanoparticles
Nanopartikel
Polymer-Wirkstoff-Konjugate
Polymerisierbare Prodrugs
Polymerization
Ringöffnungspolymerisation
Therapy
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Summary:The synthesis of polymer–drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring‐opening polymerization. The monomers polymerize into well‐defined polymer prodrugs that are designed to self‐assemble into nanoparticles and release the drug in response to a physiologically relevant stimulus. This method is compatible with structurally diverse drugs and allows different drugs to be copolymerized with quantitative conversion of the monomers. The drug loading can be controlled by adjusting the monomer(s)/initiator feed ratio and drug release can be encoded into the polymer by the choice of linker. Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self‐assemble into micelles with a long plasma circulation, which is useful for systemic therapy. Konjugate: Biologisch abbaubare Polymer‐Wirkstoff‐Konjugate wurden durch die lebende Ringöffnungspolymerisation von Prodrug‐Monomeren aufgebaut. Letztere bestehen aus einer cyclischen polymerisierbaren Gruppe, die über einen spaltbaren Linker mit dem Wirkstoff verknüpft ist. Die Polymer‐Wirkstoff‐Konjugate selbstorganisieren zu Nanopartikeln und setzen den Wirkstoff als Reaktion auf physiologisch relevante Reize frei.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201409293